


Little Red Riding Hoodie and the Sourwolf

by SourWolfie (pieprincess_andthe_fallenangel)



Category: teen wolf - Fandom
Genre: Alternate Universe - Canon, Anal Fingering, Anal Sex, Blow Jobs, Bottom Stiles Stilinski, Derek Has a Big Dick, First Time, Fluff and Humor, Halloween, Humor, Just smut, Lydia Is So Done, M/M, Panty Kink, Plot What Plot/Porn Without Plot, Sterek Week, Sterek Week 2015, Stiles POV, Stiles is Red Riding Hood, Stiles is a virgin, Top Derek Hale, Top Derek Hale/Bottom Stiles Stilinski, Underage Drinking, Underage Sex, because of course he fucking does, but everything is puppies and rainbows, derek is a beta, halloween party, kira is a cutie, pre-season 4, sterek halloween, stiles wears panties, this is basically 7k of fluff and smut, tiniest bit of angst
Language: English
Status: Completed
Published: 2015-10-31
Updated: 2015-10-31
Packaged: 2018-04-29 05:11:18
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 7,229
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5116772
Author URL: https://archiveofourown.org/users/pieprincess_andthe_fallenangel/pseuds/SourWolfie
Summary: <blockquote class="userstuff">
              <p>It had seemed like a good idea when Stiles had first thought of it… it was funny... would make everyone laugh despite all the recent deaths in their pack.</p><p>Or the one where Stiles wears a revealing little red riding hood costume to Lydia's Halloween party.</p>
            </blockquote>





	Little Red Riding Hoodie and the Sourwolf

**Author's Note:**

> Happy Halloween, my lovelies. I hope you enjoy this short, smutty, ficlet as my contribution to Sterek Week's #SterekHalloween. Unfortunately, this does conclude Sterek Week 2015. I know, it's sad. But I hope you've all had as much fun as I have.
> 
> Anyway, this ficlet is set after season 3B and is canon up until that point (a few canon scenes have been questioned though and replaced with my fanon ideas. But those are explained in the fic itself).
> 
> [Last edited to remove mistakes: 21/09/2017]

Stiles looked at the fine stretch of material in his hands and frowned slightly as he began to reconsider his choice of costume. The dress… well, that was one thing. But the black fishnet stockings he was holding and the crimson platform heels on his bed? That was something different entirely. And he didn't even want to _know_ what was inside the small, nondescript, cardboard bag that Rhonda, one of the girls that he had made friends with at the Jungle a year ago, had bought him. He had asked for her help when he first decided to wear a dress to Halloween and she had helped him to find his size in everything he needed and even leant Stiles a pair of her shoes to wear.

Stiles was thankful, he was. But Rhonda was scary sometimes and the way she had smiled at him when she presented Stiles with his present… it had sent a shiver down his spine. Stiles sighed and dropped the fishnets back onto his bed. He had tried them on the previous day and he had no idea how they were supposed to stay up for the entire night. Stiles just _knew_ that he'd be adjusting them and pulling them back up his thigh for the entire party and that could get… awkward. He flung himself onto his bed and picked up the platform shoes to try on. He hadn't asked to borrow Rhonda's shoes and he doubted he'd be able to walk in the four-inch heels he was holding. He tried them on anyway and, within seconds of standing up, promptly fell on his ass. Stiles shook his head, these things were ridiculous. He flung the shoes as far away from him as possible and grabbed his red converse out of his closet, instead.

The black bag waited on his bed and Stiles wondered, idly, if Rhonda had known he'd never be able to wear her shoes… what if she had only offered so that she had an excuse to go to his house and present Stiles with that bag?

Stiles didn't know why that bag was so scary to him. Maybe because it was so light that it felt almost empty? Maybe because he couldn't feel a distinguishable shape inside it, just a lot of crepe paper? Something about it just felt… ominous.

Maybe if Stiles changed his costume then it would give him an excuse to _never_ open the bag? Stiles sighed to himself and walked back to his bed and the gift. It was only an hour until the party, meaning it was too late to change his mind about his costume. Stiles snatched up the black object and steeled himself as he upturned it and dumped the contents.

"Oh," Stiles gasped, eyes wide, as he saw what lay on his bed sheets.

[] [] []

Stiles rang the doorbell to the Martin house and waited on the step as he tried to ignore the cold breeze on his legs, newly shaven thanks to Rhonda's insistence, and arms. He plastered on a broad smile as Lydia opened the door dressed in a sexy, yet somehow classy (maybe it was the way she did her hair?), nurses outfit. Lydia's eyes widened in surprise and she pursed her lips, probably trying to hide her amusement so as to not spur Stiles on further.

"Little red riding hood?" She asked after a moment of silence and pushed the drinks tray towards Stiles. "Seriously?"

"What? You don't think I make it look _good_?" Stiles replied and posed provocatively in a way that surely would have exposed his breasts if he, you know, _had_ any. Lydia finally broke and a wide smile reached her face as she shook her head and stepped aside to let Stiles pass.

"If anyone asks, I don't know you."

Lydia waited until Stiles nodded in agreement before she sauntered away. But Stiles knew she didn't mean it… probably. Stiles followed his friend after a few moments and entered the large living area.

"Stiles?" A woman called, incredulously, and Stiles turned his head to see Kira and Scott leaning against one of the far walls. Stiles hurried over to them at the sound of Kira's bubbly laugh; she was wearing a blonde wig with a shiny, yellow faux-leather jacket and matching trousers, her sword in a carrier on her back. She was dressed as the girl from Kill Bill, Stiles deduced. The colour was high on her cheeks and her movements wobbly, indicating that she was already drunk, as she pulled him into a hug.

"You look ridiculous," Scott laughed next to them.

"So do you."

Scott was wearing a Deadpool morph suit that was probably more revealing than Stiles' dress. Stiles still thought he should have gone with his idea of dressing up as Michael J. Fox's character in that Teen Wolf film. His best friend just shrugged.

"It was Kira's idea." And, well, yeah. Stiles couldn't fault Scott there. After a few minutes, Lydia appeared again and propped herself up on the arm of a nearby chair to talk to them. And she wasn't alone; Derek strode over with a big smirk on his face and Stiles' heart kind of froze. Derek wasn't supposed to be here! Okay, sure, he'd been invited. But no one had actually thought that he would _show up_! Least of all, Stiles.

Stiles was hit again with uncertainty and self-consciousness; the dress was much shorter than the picture had made it appear and the fishnets were absurd. It had been funny, but now he just felt exposed. For the past year, he had been trying to convince Derek he _wasn't_ a child. That he was smart, mature, and good boyfriend material… now Stiles was worried that this stupid joke had just undone all of his hard work. If he'd known Derek would be here then he would have ditched the red riding hood idea for something more classically funny, like… erm… okay, Stiles couldn't think of anything. But he would have done google searches! And he would have found something that would have made Derek laugh and not just stare at him.

"I need a drink," Stiles mumbled as he ducked his head and fled away from his friends and Derek's unrelenting gaze. He meandered into the kitchen, where all the drinks were stashed away, and his eyes zeroed in on the shot glasses almost instantly. He nodded to himself, grabbed a random spirit and started to pour himself shots. Stiles wanted to just down the bottle and drown his worries, but he knew that would do much more bad than good; he'd already embarrassed himself in front of his long-standing crush, he didn't want to make the damage irreversible. So he settled for just two glasses, instead. He shot one instantly and let the liquid courage do its job. After a few moments, he began walking back to his small group of friends, shotting the final drink as he made his way through the crowd. The alcohol burned the back of his neck before it settled, warm, in his stomach.

The ground was wobbling under Stiles' feet as he moved, distracting him enough that he didn't even notice Scott and Kira had disappeared until he was standing with Lydia and Derek again. _Wow_ , Stiles thought, _that stuff was strong_ … or maybe he was just a lightweight? It was possible, he supposed, he hadn't exactly had much time for partying lately. Stiles spun around to look for his other friends, even as Lydia was explaining that they'd gone off to dance. The room blurred for a moment as his brain lagged behind his eyes. His head was buzzing lightly as the shots continued to seep into his bloodstream. He wasn't drunk though, not yet, just on the verge.

Stiles heard the doorbell ring over the music and Lydia excused herself to go greet her guests.

"You two have fun, now," she said with a wink as she sauntered off into the crowd. Stiles grinned up at Derek, his insecurities all but forgotten.

"You think you can loosen up and have fun, Sourwolf?" Stiles asked and Derek rolled his eyes. "I'm sure I could scrounge up a costume for you somewhere." Derek looked down at his usual Henley and leather jacket combo and then to Stiles' red dress with a raised eyebrow.

"No thanks, I'm not one for dress-up outside of the bedroom," Derek muttered, _just_ loud enough for Stiles to hear. His heart stuttered in his chest and Derek's eyes were instantly drawn to the sound. But Stiles couldn't help it, okay? Derek had just implied that he was into roleplay and kinky sex! How was Stiles _supposed to_ react to that?!

"That's, er, more information than I ever wanted to know about your sex life," Stiles lied, shamelessly, before his brain reminded him that Derek would _know_ he was lying. He suddenly became aware of his arms, like he always did when he was feeling awkward, he just didn't know what to do with them, where to put them. He wished he had something to hold or anything to say so he could move his hands around aimlessly again. But his mind was still caught up on _Derek likes to wear costumes when he's having sex_!

"Oh, really?" Derek asked as he crowded in closer, his eyes roaming Stiles' body. Stiles was helpless to do anything as Derek's hands found their way onto Stiles' waist and guided him back against the wall. Derek crowded in closer still and brought his lips near Stiles' ear. "I think that you like it," he whispered clearly. Derek's hands skimmed further down Stiles' body and found the bottom of the dress he was wearing. He paused for a moment, waiting to see if Stiles would object, before Derek's fingers gently slipped underneath the soft material and traced their way slowly up Stiles' thighs. "I think it turns you on." And _oh God_! Was this really happening? Was Stiles dreaming? Hallucinating? Had Lydia put something in the drinks again?

Stiles didn't say anything, just shuddered as Derek's fingers brushed his upper thighs. His throat felt dry and he was becoming very aware of the fact he was steadily becoming aroused in an outfit that Stiles was sure would show _everything_. Then he remembered he was _in public_. No-one was paying any attention to them but he was most definitely still in a room filled with at least 20 people as _Derek Hale_ was stroking his thighs, thumbs inching _extremely close_ to his crotch. Before Stiles could find a way to ask to go someone more private, Derek was purring into his ear once more.

"How about we go upstairs?" Derek asked and Stiles nodded fervently. Derek stepped back and began to walk away without another word, leaving Stiles to chase after him. After they had got out of the room though and into an empty hallway, Stiles found Derek waiting for him at the bottom of the stairs. Stiles walked closer to him, feeling a little lost. He hadn't even known that Derek _liked_ guys and now they were going to… what? Make-out? Grope each other in one of the upstairs bedrooms? …More?

Stiles didn't have much time to question it further before Derek's hands were on him, pushing him up against the nearest wall, like he had done many times before. But unlike all the other times, he kept leaning forwards until their lips were meeting in a passionate kiss. Stiles' hands instantly ran through Derek's hair and fisted it in between his fingers, like he'd wanted to do for over a year. It was soft to touch. A little bit of gel made the ends stiff, but it didn't feel tacky. Derek's body was pushed flush against Stiles', which was both hot and pretty embarrassing, actually, considering he was already half hard from the not-really-groping that had occurred only moments ago.

Stiles loved the contrast of Derek's soft lips and the coarse scratch of his stubble as they kissed up against the wall in the entrance hallway. It burned against his face and made him feel _alive_. It was just as rough and perfect as Stiles had secretly been hoping for. Derek's hands were on Stiles' waist and bunching up the tight material of his dress. There was another ring of the doorbell a few feet from them and Derek growled deep in his throat before pulling away. Stiles, pathetically, tried to chase Derek's lips as he moved and was disappointed when he couldn't meet them again. But Derek just grabbed Stiles' hand in his own and pulled gently as he began to guide Stiles' up the staircase. Stiles got the idea and followed happily, staring down at where his hand was clasped securely inside Derek's.

Derek didn't bother trying any of the bedrooms and Stiles wasn't surprised, even his weak human ears could hear the pounding on bed springs and low groans that echoed from them. Stiles started to feel disheartened as Derek just kept pulling him down the corridor. How were all of these rooms taken _already_? The only rooms remaining were Lydia's bedroom and the posh upstairs bathroom that had only just been refurbished. And Stiles knew that Lydia kept both of those locked. But Derek just stopped outside the bathroom and opened the door with a key. Stiles squinted, unsure how he had managed to get a hold of that and was about to ask when he was being dragged into the large room. Derek threw the key onto a pile of towels to the right and twisted the lock on the door once they were both inside. He didn't waste any time in reclaiming Stiles' mouth, either.

Derek nipped and licked at Stiles' lips as his hands roamed over Stiles' body, inching very close to his dick which was extremely hard and aching. But it wasn't until Stiles felt Derek's erect dick press against his thigh until he realised that this was _actually_ happening. Stiles' eyes shot open and the next time that Derek pulled back from his lips to work on his neck or jaw, the words tumbled from Stiles' mouth.

"I'm a virgin," Stiles blurted out and Derek froze from where he'd been licking a kiss into the underside of Stiles jaw. Derek began to slowly pull away and Stiles cursed himself. He hadn't meant for Derek to stop… he just thought that he deserved to know. _It was a bad idea_ , Stiles realised, _such a very, very bad idea._

"I thought that you and Malia…?" Derek whispered, leaving the question open to drift into silence. Stiles shook his head.

"Nope. No, that, ah, almost happened but we were in the basement of a mental hospital so I didn't exactly have a condom at hand and, you know, Sheriff's son, here. Practicing safe sex was schooled into me the second that I knew what my dick could do." _Yeah, Stiles, that's perfect_ , Stiles thought to himself, _remind the guy who wants to touch your dick that your Dad is the sheriff and will probably shoot his ass for ever going near his underage son_. "And it was probably a good thing too…" Stiles said into Derek's silence.

Stiles forced himself to stop talking and resigned himself to wait for Derek's reaction. He was expecting Derek to back away even further, put distance between them. But he stayed completely still, crowding Stiles against the door just as much as he had been a minute ago. Stiles fidgeted and avoided Derek's gaze. A moment later, though, Derek's lips were back on his own. The kiss was slower, but it took Stiles' breath away just as much as the first one had because he wasn't expecting it.

"Do you still want to do this?" Derek asked as he pulled away and Stiles nodded enthusiastically.

"Yeah, yes, definitely," Stiles responded immediately and Derek laughed as he resumed working on Stiles' jaw. Stiles knew he would have wicked stubble-burn soon and wondered if Derek was going to add hickeys to the show. "But… just… why do _you_ still want to?" Stiles eventually couldn't stop himself from asking.

"Everyone has to start somewhere," Derek said as he slowly pulled his lips away from Stiles' skin. He gave the younger boy an appraising look before kissing him again. "Turn around," Derek whispered into Stiles' open and pliant mouth. They pulled back from each other a moment later and Stiles smirked but did as he was told.

"You're very direct to the point, aren't you," Stiles teased breathlessly. Derek's hands ran up Stiles' side and to his shoulder, very slowly. He pressed an open kiss on the back of Stiles' neck as his hands found the zipper on the dress and began to inch it down.

"You look ridiculous in this," Derek murmured into the exposed skin before biting down delicately at the area he'd just been kissing. Stiles shuddered.

"You didn't seem to mind," he replied as his voice shook and Derek huffed.

"Maybe I think ridiculous looks good on you." Stiles laughed breathlessly, he couldn't believe this was a conversation he was actually having as Derek slowly undressed him.

"Are you sure you don't just have a kink for women's clothing?" Stiles asked playfully and Derek was so close behind him that he could feel the brush of his shoulders as Derek shrugged.

"Maybe."

Derek had finally got to the bottom of the zipper and his hands slipped back down low to the hem of Stiles' dress. He began to pull the material up slowly as the palms of his hands brushed up against Stiles' soft skin. Derek's hands stilled against his waist, though, as he felt the delicate material covering Stiles' ass. Stiles could hear Derek swallow thickly behind him as he dropped the dress back and placed his hands wholly on the silk panties that Stiles was wearing underneath his red riding hood dress. Derek rubbed at the material on Stiles' sides.

"What are _these_?" Derek teased. But his voice was different, no longer calm but instead, it sounded rugged, _wrecked_. Derek sounded completely turned on and Stiles couldn't believe how attractive that was.

"A present from a friend," Stiles answered breathlessly and Derek spun him back around, crowding him up against the wooden door. Derek was growling low in his throat and it made Stiles' dick jump. He was completely turned on, at this point, his dick straining against the soft fabric. Derek kissed him again, this time a little more rushed and sloppy. His big hands re-found the hem of the dress and quickly tugged it up and over Stiles' head, only detaching their lips when _absolutely_ necessary to remove the garment. Derek threw the red dress back and over his shoulder before looking down at Stiles' entire body. Stiles looked down nervously and frowned at his skinny body. But, for once, he wasn't so worried about his lesser muscle density. It didn't seem like it was bothering Derek, whose eyes had wandered happily over Stiles' body for several seconds before resting on the bright red undergarments that were attached with fine, red lace suspenders to the top of the fishnet stockings that Stiles was wearing. They were surprisingly comfortable, softly caressing his junk.

Derek's eyes flashed a bright blue and Stiles shuddered under the weight of Derek's gaze. Self-consciousness was beginning to creep in and Stiles itched to cover himself up somehow. But before he could make any movement, Derek was dropping to his knees. Stiles stared down at him with an open mouth. _Derek Hale is on his knees in front of my dick_ , Stiles' brain shouted before short-circuiting. And then it wasn't just the teasing looks and touches anymore. Derek's tongue flicked out and lazily traced the very visible outline of Stiles' dick through his red silk panties.

Stiles gasped out a loud and lewd groan in response and barely stopped himself from bucking his hips forward in search of _more_. Derek rested his palms on Stiles' hips as he continued to lick and kiss at Stiles' erection through the soft material. Stiles' legs wobbled underneath him and he prayed they wouldn't collapse.

"I'll mark that down as a definite _yes_ for _panty kink_ , then," Stiles whispered and Derek huffed a warm breath over the wet fabric, which created a slow shiver that ran all the way up Stiles' spine. Derek continued to lick and kiss at the dampening fabric entrapping Stiles' erection until Stiles was a whimpering mess above him. Stiles fisted Derek's hair in his hand and _pleaded_ for more. Eventually, Derek tugged at the waistline of Stiles' panties and slowly pulled them down and out of the way. Stiles' dick sprung free and the younger boy moaned as the cool air hit it. Derek's long thick hand wrapped around the base of Stiles' dick, his thumb moving in slow, concise circles underneath the weeping head. Derek lowered his mouth to Stiles' dick and flicked his tongue out momentarily to lap up the pre-come dripping from the tip. Stiles shuddered and his knees threatened to give out on him as he watched Derek's slow movements. He held his breath as Derek opened his mouth and brought it down to cover the head of Stiles' dick. When he finally managed to exhale again, it came out as a long, lewd moan.

Derek sucked at the apex of Stiles' dick with abundance but, despite Stiles' begging for _more_ , he never let his mouth go lower than the head. Stiles could feel his dick throbbing to be brought to completion, but Derek didn't want this over so quickly. Derek pulled off with a wet pop and _finally_ licked up Stiles' dick, tracing a thick vein all the way from the base to the apex. Stiles closed his eyes as a deep shiver wrecked its way through his body. But then Derek was standing up and moving away.

Stiles' eyes shot open and he stood up fully from where he'd been leaning against the door. Stiles was halfway through an unplanned complaint when he saw Derek open up the bathroom drawers and start rummaging through them.

"What are you looking for?" Stiles asked and Derek paused for a moment, looking over to Stiles with one eyebrow lifted high on his forehead.

"Something we can use for lube," Derek said as if it was obvious, and yeah, Stiles supposed it kind of was. Stiles looked down at his own body as Derek continued to search. He was still wearing his stockings and his trainers, but his panties were pushed down to the middle of his thighs. He thought for a moment about what to do and eventually kicked off his converse and pulled the rest of his clothes off of his legs. By the time he looked up again, Derek was shutting the drawer with a bottle of lotion in his hand.

"I really don't think I should be the only one naked, right now," Stiles said, indicating at Derek's fully clothed body with his hands as he talked. Derek looked down at himself before chucking the bottle he was holding towards Stiles. Stiles struggled to catch it, almost dropping the bottle with the anticipation and nerves making him feel weak all over. Stiles stayed completely still as he watched Derek shrug off the leather jacket and drop it to the floor. And he was full on gaping as Derek grabbed the bottom of his shirt and tugged it up and over his head. Stiles was so engrossed in watching the pull and twist of Derek's abs, that he barely noticed the jeans get pulled off. But his eyes focused again as he noticed Derek's hands playing with the waistband of his briefs. Stiles swallowed thickly as Derek made eye contact and deliberately made a show of inching the fabric down. And then he was naked. They were _both_ naked. And hard. And just _staring at each other_. Stiles' heart was racing as he soaked in every detail and tried to not let the bottle of lotion fall through his fingers. He never knew that he could be so captivated by someone before. Derek approached gradually, letting Stiles take his time. Stiles' eyes dropped to Derek's dick and he smiled faintly. It was uncut and thick and large but, thankfully, not too large. It was probably the perfect size and Stiles' itched to touch it, to feel Derek's foreskin move underneath Stiles' fingers.

Instead, when Stiles reached forward, it was to grab the nape of Derek's neck and pull him in closer for another kiss. Derek opened his mouth to it instantly and pulled their bodies closer in the same instant. Stiles gasped as he felt his dick come into connection with Derek's.

"Do you have a condom?" Derek asked as he took the bottle from Stiles' slack fingers. Stiles thought for a moment and felt disappointment sink in as he realised that he hadn't even thought of a condom and he _definitely_ didn't bring one. Stiles shook his head sadly but Derek didn't seem deterred as he sucked a kiss onto Stiles' neck. "That's okay," he muttered. "We don't actually need one, my metabolism is too fast to catch or spread anything," Derek concluded and Stiles tried to let that information sink in. But his brain was floating in the feeling of Derek's tongue and teeth against his neck. He figured that Derek was probably giving him a hickey… he'd never had a hickey before. This sharp and teasing pleasure was _not_ what he'd expected it to feel like.

Derek pulled back and looked at Stiles questioningly.

"Stiles?" He asked like he was waiting for the answer to a question. When Stiles didn't respond, mainly due to the fact he had _no clue_ what Derek was looking for, Derek continued to talk. "Are you okay with that?"

"With what?"

"With not using a condom," Derek clarified and Stiles nodded minutely, paused, and then nodded vigorously instead as he attempted to get the idea across of just _how much_ Stiles was okay with that. And anyway, even if he _did_ have a condom, Stiles wasn't sure it would fit Derek's dick. Derek held him close and kissed Stiles' neck as his hands wandered down his body to his waist. "It's a shame though… I don't want to get come stains on those panties of yours," Derek teased and grabbed Stiles' ass with his free hand.

"You really do have a women's underwear kink, don't you? Not that I'm complaining. Hell, I may never wear boxers again if this is how you react to panties." Stiles imagined them sitting around in normal everyday situations and teasing Derek with the fact he was wearing women's underwear, but that they would have to hold off from touching each other until they were somewhere more private. Derek growled deeply into Stiles' ear and it made him shudder with anticipation. "Shall I… turn around?" Stiles asked, swallowing thickly. Derek nodded and so Stiles stepped back and turn around, ready to go back to leaning against the wooden door. But Derek instead guided him to the counter and Stiles leant over that instead, giving Derek a better access to his hole. Stiles knew that he was already a little bit loose due to some personal time he'd spent with himself and a dildo a few hours earlier. But he still felt a little nervous as he felt Derek's presence behind him and heard the pop of the bottle cap being opened.

There was a sound of the lotion being squeezed from the bottle and then one of Derek's hands was on Stiles' lower back, making calming circles in the tense muscle.

"Shhh, it's okay. I won't hurt you," Derek said in a voice Stiles had never heard from him before. It was relaxed and calm and reassuring. Stiles looked up from where he was staring at the countertop and made contact with Derek's eyes in the reflection of the mirror in front of him. His face was open and warm while maintaining concern in his features. "I can stop if you…"

"No," Stiles answered immediately. "Keep going." Derek nodded and didn't question any further. The hand on Stiles' back kept up the calming movements as Derek's other hand lowered to Stiles' hole. Stiles felt the press of a lubed finger against his rim and tried to relax. Derek's finger didn't push any further, he just stayed there, playing with the tight ring of muscle as he allowed Stiles calm down. It wasn't long before Stiles was completely relaxed and complaining at Derek's teasing, pushing back against Derek's hand. Stiles whimpered as Derek's finger played with his sensitive hole as Derek laughed light-heartedly behind him. After a few seconds, Derek gave in. He pushed his finger slowly past Stiles' rim, making Stiles gasp quietly. Derek began to slowly move his finger in and out of Stiles' hole before adding a second and third in. Stiles blushed but was thankful when Derek didn't comment on how obvious it was that Stiles had opened himself up not long ago. Talking to Derek about touching himself would be nothing short of embarrassing.

Stiles let out a pleased moan and bit down on his bottom lip as Derek continued to fuck him with his fingers. He pushed back against Derek's hand unconsciously, as he begged for _more_. Derek eventually conceded. He slowly removed his fingers from Stiles' hole and coated his dick in the lotion. He lined his dick up against and slowly began to push inside.

" _Derek_ …" Stiles whined as Derek took too long. Derek shushed him gently.

"We have to go slow," Derek whispered. "It's your first time, I don't want to hurt you…"

"Oh come on," Stiles snapped. "I think it's pretty obvious that you aren't the first thing I've had inside my ass," Stiles continued to insist as Derek finally bottomed out and paused. Derek laughed breathlessly against the skin of the back of Stiles' neck and Stiles shivered in response.

"Fucking yourself with a vibrator isn't exactly the same thing…" Derek muttered and Stiles refused to outwardly agree because he just wanted Derek to _move_! But, yeah, he'd already figured that out. Derek's dick was thicker and longer than any dildo that Stiles had ever used. It stretched him out more tightly, filled him up more completely. Derek reached depths inside Stiles that his dildo never could and, yeah, it hurt a little bit… but Stiles knew that it'd feel amazing soon.

Derek eventually began to move his hips in and out. It was slow at first. Stiles whined some more and pushed his ass back against Derek's dick. Trying to get… _more_. But Derek grabbed his hips tightly inside his large hands and held Stiles in place.

"Derek, _please_!" Stiles moaned louder and Derek huffed behind him.

"Stiles… you're making this very hard on me."

" _Good_ ," Stiles responded without pause, a smirk plastered on his face. Stiles looked up and caught Derek's eyes in the mirror in front of him. Derek was giving him a look that could only be described as a bitch face, glaring Stiles down for twisting Derek's words into a euphemism. Stiles found that the bitch face wasn't quite as effective when Derek's dick was buried in his ass. He decided to say so and opened his mouth to make the sarcastic comment when Derek thrust his hips sharply forward and drove his dick deep and hard into Stiles' ass.

Stiles' words were lost in his breathy moan as his eyes slammed shut and he clung tightly onto the countertop. Derek laughed quietly behind him as he slowly pulled out and slammed back in again. Stiles continued to whimper and mutter as he writhed against the counter, begging for more, faster, harder… and Derek eventually gave in.

Derek grabbed Stiles' hips forcefully as he thrust in and out of Stiles' tight hole. Stiles pushed backwards to meet each of Derek's thrusts as they both let out a stream of expletives. The dildo was good but this was no comparison. The angle that Derek could get, how deep he could go in… it was so much better than anything Stiles had been able to achieve on his own. Derek pushed against Stiles' back and encouraged Stiles to bend over more, giving him the perfect angle at Stiles' prostate. Stiles let out a loud, lewd groan as Derek drove hard against it and he clapped his hand over his mouth in surprise.

"Don't…" Derek pleaded as Stiles tried his best to keep quieter. "I like hearing you," he admitted and Stiles groaned loudly in response. He didn't know that could be such a turn on. Stiles' eyes fluttered open and he looked up at the mirror in front of him. He couldn't see much, it wasn't at the right angle, but he could see Derek. He could see Derek leaning over Stiles, one hand holding his hip, the other gripping the countertop until his knuckles were white. A small sheen of sweat made Derek's muscles glisten as they contracted and relaxed with every thrust. Stiles didn't know how he could be so lucky to have Derek on top of him but he thought that, if he died tonight, he would die happy.

Stiles' dick jumped against his stomach, as Derek let out a particularly erotic groan, and he itched to take himself in his hand and bring himself to completion. He felt like he was going to go crazy if he didn't come soon. But he also didn't want to let this moment end too early. He wanted to bask in it forever. Unfortunately, Stiles didn't have much choice. It was only another minute later when he felt his orgasm building in his groin. He whimpered and moaned and cried out Derek's name as he toppled over the edge and came all over the counter he was leaning against. Stiles basked in his afterglow as Derek continued to drive into Stiles, chasing his own orgasm. Stiles met Derek's thrusts as he encouraged him to keep going and eventually Derek was coming inside Stiles' ass. He thrust twice more to milk himself clean and then they both collapsed. Derek wrapped his arm around Stiles' waist and pulled them both down to the floor. Stiles sat half on the floor, half on Derek's lap, as they leant against the wall and breathed heavily, both exhausted.

"That was…" Stiles started, but he was too lost for words. "Just… _wow_. Amazing… I literally have no more words to describe how amazing that was. Seriously, just… I can't fucking _wait_ to do that again!" Stiles exclaimed and after a second he felt Derek freeze up underneath him. Stiles' heart began to sink. He knew what was coming before Derek even opened his mouth.

"Stiles… This was-"

"Don't you dare say this was a mistake!" Stiles interrupted angrily and Derek shut his mouth for a moment.

"Fine. Mistake… isn't the right word. But it can't happen again."

"Why not?" Stiles insisted, as he twisted around to stare accusingly at Derek, whose arms were still wrapped tightly around his waist. Stiles wasn't angry anymore, though. He was sad instead, he'd let himself get his hopes up that they could be something. But it hadn't even been five minutes since they'd had sex and Derek was already backpedalling.

"Because… it's illegal," Derek said. But it sounded more like it was a question than anything assertive.

"No more illegal than what we _just_ did," Stiles announced. He wanted to pull out of Derek's arms and make himself appear confident and independent… like Derek choosing to stay away from Stiles was little more than a nuisance. Guys like that kind of confidence, didn't they? But in the end, Stiles didn't have the willpower. He _liked_ being held by Derek. And if this really _was_ the last chance he would get at being held like this, then he wasn't going to throw it away just because of his pride.

"Look, Stiles, I _like_ you. I do. I mean, I think that's pretty obvious after what we just did…" Derek concluded and Stiles felt the urge to laugh at his dry attitude and then immediately hated himself for falling even deeper for Derek when the guy was literally saying that they couldn't be together. "But we can't have sex again. You're _seventeen_. It's just… too risky." Stiles had to give Derek that, it was risky. Stiles' Dad could, and probably _would_ , throw Derek in a cell and eat the key if he ever found out that they were having sex.

"You know, there are a lot of people who have relationships that _don't_ revolve around sex. And, well, if _you're_ not going to be having sex and _I'm_ not going to be having sex, then we might as well be not having sex… together?" Stiles rambled and Derek looked at him with a blank look for a moment before finally answering.

"Is that your attempt at trying to ask me out?"

"Trying but… not really succeeding." Derek looked at Stiles for a moment longer, in complete silence, before a small smile began to form on his lips.

"…I wouldn't say that."

Stiles stared at Derek dumbly, eyes wide with surprise. He hadn't actually expected that to work… in his mind, Stiles had already resigned himself to awkward pack nights where they both tried not to look at each other as they pretended that Derek hadn't taken Stiles' virginity and broke his heart. They stared at each other for a few seconds before Stiles noticed Derek's eyes drift down to his lips. Stiles leaned forward at the same moment that Derek did and their mouths brushed lightly in a delicate kiss. Derek bit Stiles' bottom lip as he pulled away. They stayed completely still for a moment, eyes closed as they leant their foreheads against one another and breathed slowly. Stiles moved forward again after a moment and captured Derek's mouth in another kiss. This one was a little more erotic. Stiles' mouth opened as his tongue brushed against Derek's lips. Derek allowed the kiss for a further few seconds, without opening his mouth to it, before he pulled back. Stiles tried to chase him but to no avail.

"Stiles, we're naked," Derek whispered and Stiles' eyes snapped open. He'd somehow managed to forget. Stiles tried to not to be affected by his self-conscious habits and shrugged cheekily, instead.

"So?"

"So, I think making out with you while we're both naked goes against our 'no sex until you're eighteen' rule." Stiles wanted to argue, but he couldn't deny Derek's point and so he slowly pulled himself off the floor instead. Derek loosened his arms from Stiles' waist and let them fall slack as Stiles stood up and walked over to his clothes. "Wait," Derek called out as Stiles grabbed the red panties off the floor. "You need to clean up first," Derek said as he stood up. Derek went to grab a towel but then thought better of it and rooted around until he found some makeup wipes in one of the drawers. He took out a few wipes and Stiles held out his hand for them but Derek shook his head. "Turn around," Derek muttered and Stiles began to chew at his bottom lip as his eyes drifted from the wipes to Derek's face and back again.

"I can..." Stiles began to say but he gave up when Derek just looked at him with one eyebrow raised high on his forehead. Stiles turned around and allowed Derek to clean the come off of him. When Derek was done, he turned Stiles around and cleaned the come off his stomach, too.

"There," Derek said, placing a quick kiss on Stiles' cheek before stepping back. Stiles blushed as Derek's eyes swept over his body. It felt like Derek was trying to commit it all to memory, knowing that he wouldn't see Stiles naked again for months. Stiles was checking Derek out for the exact same reason. His eighteenth birthday suddenly just couldn't come quick enough.

After a moment, Derek turned away and grabbed his briefs off the floor and so Stiles resumed his attempts to put his panties back on. He got the thin fabric covering his junk completely before hiking his stockings back up his legs. Stiles' clumsy fingers fiddled with the stockings as he attempted to attach them back to the panties. But then Derek's hands were sliding over his own. Stiles looked up and smiled at Derek's face as he concentrated on securing Stiles' underwear. Eventually, when Derek was done, their eyes met and they both smiled at each other stupidly.

"Thanks," Stiles whispered and Derek nodded before placing a soft kiss on Stiles' lips.

They finished getting changed in easy silence, Stiles struggling with the zip on his dress as Derek cleaned up any mess that they'd made in the bathroom. When they were both ready, Derek took Stiles' hand in his own and led him out of the bathroom, locking up before they moved on. Stiles stared down at the key in Derek's other hand, curiosity burning.

"So… the key?" Stiles finally asked as they made it to the top of the stairs and Derek, _honest to God_ , blushed.

"Lydia gave it to me when you left to get a drink, with a warning to clean up after ourselves… _or else_." Stiles took a moment to let that sink in and then groaned in annoyance.

"Oh _great_ ," Stiles muttered sarcastically and Derek frowned as he looked over at him.

"What?" Derek asked carefully. Stiles noticed the grip on his hand start to loosen and he shook his head and grabbed on harder to Derek.

"It's just… Scott is going to be so annoyed when I tell him about us and he finds out that Lydia already knows." They were at the bottom of the stairs now in the fairly empty hallway, when Derek paused. Stiles looked at him with suspicion.

"Scott already knows too," Derek said quietly and Stiles' mouth dropped open in surprise. How did he already know?! Surely Lydia hadn't said that stuff to Derek in front of Scott… "You were pretty loud…" Derek answered Stiles' unasked question and Stiles wanted to facepalm. Of course… werewolf hearing… how could he forget? Stiles gnawed some more on his bottom lip as he thought everything over. All his friends likely already knew about him and Derek by now. But that wasn't so bad… Sure, he didn't get to see the look on their faces as he announced to them that he had successfully worn Derek Hale down into dating him… but he could live with that, he decided as he looked down at where his hand was clasped with Derek's.

"Emphasis on pretty?" Stiles asked with a teasing smile and Derek rolled his eyes before they started walking back into the main room again.

"You're an idiot," Derek announced playfully.

"Yes, but I'm a _pretty_ idiot."

Derek looked down at him and smiled and this right here was everything that Stiles had wanted for the longest time. The smiles, the handholding, the tentative promises of happiness and something _more_. Yeah, Stiles could get used to this.


End file.
